Really good questions

I found an old note recently with a set of really good questions I’d like to share with you. I think most of these came from Seth Godin. He has one of the best podcasts ever made.


What would you do if you knew you were going to succeed?

What would you do if you knew whatever you were going to do you would fail? What is the process you would choose to take, if you knew you were going to fail?

Whatever is causing you stress at the moment, be it a business or a relationship… anything, what might this look like if it were easy? If it had to be easy,  what might it look like?

How far can you ratchet down the scale until you have no more excuses to do something? For example exercise may seem overwhelming, how far down until it becomes easy and you no longer have an excuse not to do it?

Where can I selectively de-optimize activities to promote wellness and optimize myself overall?

Essence of design theory: “Who’s it for?” and “What’s it for?”.

What would matter when you’re 90?

What would you tell your best friend to do in this situation?

What are you getting out of the cycle of [something]? What does it do to add to your life?

What if you stopped looking for new ideas and simply focused on the best idea you have right now?


Sometimes the best advice comes in the form of questions, as they cause us to pause and think about our next steps rather than just telling us where to walk.

Change the thinking to change the outcome

When we do anything, when we think anything, we do so through a lens crafted from a mosaic of our values and beliefs. These values and beliefs influence our thinking and how we perceive the world so much that to us, they have more meaning than the truth. If the truth is at odds with our values, chances are we will double down on what we believe to be true rather than what is objectively true.

This can really get in the way when we start trying to deal with our problems and challenges in life. No matter what we try, we can never break the cycles.

We cannot solve our problems with the same thinking we used when we created them.

– Albert Einstein

Although this quote is generally attributed to innovation and technology, it can challenge a thinker to look at any problem from a different perspective. If pushing doesn’t work, try pulling.

Einstein’s quote highlights a key truth: the thinking that created a problem won’t be the thinking that solves it. It calls for a shift in mindset. Real solutions require us to challenge old patterns and embrace change.

To do so will feel very strange at first. In fact it will feel down right wrong. We will need to completely go against what we’ve “always” felt to be true and what we’ve connected to our very identities.

Change starts with action, and it happens incrementally. It happens so slowly we barely notice. Taking action and d”oing something” will eventually help you get more comfortable with the new way of thinking. The more you engage with the new approach and stay aware of it, the more it begins to shift your old thought patterns. Over time, this new perspective becomes part of how you think. Either you’ll start seeing different results, or your expectations will shift enough that the issue no longer feels like a problem.

The mindset that built it won’t fix it.